


Days 1-5

by FPwoper



Series: 31 days of... ships [1]
Category: Supernatural
Genre: I guess I'm trying this, Kinktober 2019, M/M, Multi, Ships also given per drabble, Suptober 2019, Warnings/Tags given per drabble!
Language: English
Status: Completed
Published: 2019-10-02
Updated: 2019-10-05
Packaged: 2020-11-10 17:14:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 3,698
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20855366
Author URL: https://archiveofourown.org/users/FPwoper/pseuds/FPwoper
Summary: Hopefully 31 different short drabbles related to the Supernatural fandom!Prompts taken from Suptober 2019 and/or Kinktober 2019.Warnings are in the chapter notes as they might differ! (marked explicit just to be safe)I'VE CHANGED THIS INTO A SERIES TO ALLOW FOR BETTER TAGGING, SO FROM DAY 6 ONWARDS THEY ARE PART OF THE SERIES "31 DAYS OF... SHIPS" RATHER THAN THIS WORK!





	1. Day 1: Autumn/Wax play

**Author's Note:**

> Let's see how long I can keep this rolling.  
Day 1 prompts: Autumn [suptober] and wax play [kinktober].
> 
> Mature, Destiel, artist!cas

Autumn has always been special to Dean – it reminds him of when him and Cas first got together. This year, he figures that he can finally ask for something he’s been wanting to do for years.

“Did you get your inspiration from the candles, Dean?” Cas asks, and Dean can’t help but blush. He might have been inspired by those candles, yes, but it’s not the main reason he wants to try wax play.

“I’ve been looking at a lot of your art, and I know you’ve been wanting to do that with a human canvas, and…” Dean trails off, blushing dark.

“And what, Dean?” Cas says. His eyes are dark and are focused intensely on Dean’s face. Dean is only slightly intimidated. He takes a deep breath.

“AndIdon’twantyouseeingotherpeoplenakedandputtingartonthem.”

“Very clear, thank you, Dean.” Cas seems to get the gist, though, but Dean wants to be able to express whatever it is that has been bothering him.

“I don’t want you and other people naked.” Dean bites his lower lip. “I mean, I don’t want you to put your beautiful art on other people.”

Cas’ face does the weird thing where it’s all smiles, crinkly eyes and all, and Dean knows that his weird request will be honoured – Cas’ Pollock-like art on his body, but in wax. If it’s any good, he’ll even allow Cas to take pictures and show them off. Dean doesn’t care – he’s simply excited about all this.


	2. Day 2: Eyes/Body Switching

**Summary for the Chapter:**

> Pairing: DeanCasJimmy  
Rating: mature  
Tags: Witch!Cas, Witch!Dean, Witch!Jimmy, body swap
> 
> Suptober day 2: Eyes  
Kinktober day 2: Body Switching

**Notes for the Chapter:**

> Annnnndddd day 2!!

When Dean woke up way too early on a Thursday morning, he was vaguely confused. He couldn’t pinpoint exactly why he was confused, just that something was _wrong_. It was only when he stepped out of bed that he realised exactly what was wrong.

… Those legs didn’t belong to him. His leg hair was much lighter, and he frowned in confusion.

His brain, still half-asleep, didn’t connect the dots until he actually stared at his eyes in the mirror. Or well, not his eyes, exactly. _Jimmy’s _eyes. He blinked slowly, first thinking how the fuck he should know these eyes were Jimmy’s, specifically, and only then his brain got to the main event. Why was he in Jimmy’s body? Was this some sort of weird dream? What the hell was going on?

Dean turned slowly and left the bathroom again. He felt weird peeing when it wasn’t his own dick he was holding, even though he’d held the dick often enough. Dean swallowed uneasily and moved over to the bed, where he saw himself and Cas, still asleep, lying peacefully.

“Fuck,” Dean muttered. He sat on the edge of the bed and pretended he wasn’t freaking out, and it was only when he heard someone say “Dean” in his own voice that he acknowledged that this was spectacularly messed up. Of course Cas was in his body. At least Jimmy would have it relatively easy while being in Cas’s. He’d just get confused over the tiny differences between his own body and Cas’s.

“I think something went wrong with last night’s spell,” Dean said hoarsely, without looking up.

Cas was always one of the quickest, and it didn’t take long until Dean heard swearing from Cas’s general direction. “You could say that,” he grumbled after the swearing stopped. “I love your bow legs, Dean, but never intended to actually find out first hand how that walking thing works on these wonky legs.”

“You tell me,” Dean said. “Straight legs aren’t fun either if you’re not used to them.”

Castiel sighed and Dean joined him in the simple action. “I guess we should wake Jimmy and figure out how to fix this, right?”

Dean nodded. “Preferably before I have to pee. I love Jimmy’s cock, but don’t think you could honestly stick it in me after I’ve used it to pee, myself.”

“Let’s get to work, then!”


	3. Day 3: Royalty/Tentacles (+Mantis)

**Summary for the Chapter:**

> When crown prince Dean disappears, it's big news....
> 
> Suptober day 3: Royalty  
Kinktober day 3: Tentacles  
\+ Bonus prompt: Mantis (see notes)

**Notes for the Chapter:**

> Look, I found this amazing, amazing prompt list today on tumblr. I want you guys to simply take a look at it: [HERE](https://fpwoper.tumblr.com/post/188114771761).
> 
> Pairing: Dean/cas/jimmy  
Rating: explicit  
Warnings: octoman!Cas, octoman!jimmy, royalty!dean, double penetration, consentacles, suspend disbelief, mantislaughter

One day, prince Dean Winchester, the crown prince to the kingdom, disappears. It’s big news, and everyone is lost. The fact that Sam has been unusually quiet is lost in the general panic about the disappearance of his brother, and no one thinks to ask the other prince if he knows something, assuming he’s just as lost as everyone else.

Sam knows, though. Sam knows where Dean is.

****

Dean has always been a fan of the ocean. When his mother, the Queen, was still alive, she used to take both him and Sammy down to the beach any time she could, and Dean has kept taking Sam down there after her death, to honour her memory. The King had never been a big fan of the sand and water, but encouraged them to keep the memory of their mother alive by going to the ocean. Sam lost interest when he turned eight and learned how to read, but Dean religiously kept going any time he could leave court.

He knew that he would have to say goodbye to his regular visits at some point, since he was going to be a king and take over after his father, but he didn’t want to. So he keeps going, even when his lessons become more demanding, even when he takes over some of his father’s duties.

He keeps going, because he’s met the loves of his life at the beach and cannot possibly ask them to leave the ocean for him.

The first time Dean met Cas and Jimmy was when he was only nine. His mom had just died, and he was mourning her, missing her immensely when he went down to the beach. He only barely remembers how it happened, but he was sitting on a pier with his feet in the water, probably crying, and he suddenly felt something touch his ankles. He almost pulled out, but didn’t, and was happy for that, because the faces looking up at him were kind. And identical. Looking back at that meeting, where Cas and Jimmy only held his ankles, basically, Dean knows that was probably when he realised that he liked boys too.

Now, years later, their relationship has much evolved – Dean has managed to save up his allowances and buy a house on the shore. He’s in the process of slowly modifying it so the twins can actually enter, too, but he’s effectively moved in there, and his prized possessions, the ones he actually cares about, are all in the house at this point. He’s ready to disappear forever. Sam knows about the plan, Sam has known since things between Cas, Jimmy, and Dean had turned _serious_ and… physical, since he’d accidentally spotted them going at it, but Dean knows that Sam is okay with it and is actually looking forward to taking over Dean’s position.

No, Dean is going to put his plan into motion in a few days and will disappear forever, only for a village a few kilometres from the palace to gain a new hermit, one that will not draw any attention to himself and will probably only be known as a part of the stories about the tentacled men that sometimes appear near the shores of the village. He will not even need to buy many groceries in the village, since the twins provide him with seafood and he has been growing his own vegetables for a while now. Dean is all settled to disappear.

****

When he arrives at his new home, the twins are waiting for him. They’ve caught a mantis somehow, even though those animals are supposedly not at all easily killed. Both Castiel and Jimmy are… _very good _with their appendages, though, and honestly, Dean should not have been at all surprised at this turn of events. He makes quick work of making himself some dinner and sits out on the pier near his home, legs dangling in the water again. Jimmy and Cas have attached some of their suckers to Dean’s bare legs and slowly massage the flesh while Dean enjoys dinner. They’re quiet this evening, as if they know that this is a turning point in their relationship, and they are simply enjoying the quiet before the storm.

After dinner, though, Dean puts his plate in the sink in his home and brings a towel outside. After dropping his clothes and the towel on the pier, he lowers himself into the cold ocean, where the twins are waiting for him. They will take care of him, Dean knows, and he knows it well.

They are floating in the ocean, and Dean knows that anyone who looks out would be able to see them, but he doesn’t care, and despite the cold, his cock quickly hardens as the twins’ tentacles move over his body, latching on to his nipples and hips. Castiel is sucking marks onto his neck, too, and Jimmy is slowly opening Dean’s hole with the fluid he produces that’s apparently waterproof. Dean has stopped trying to ask the twins about it, since apparently it’s something natural that they can’t really quite explain, so he just takes it for granted.

One of Jimmy’s smaller tentacles slowly breaches Dean, and Dean sighs in relief. “Please, Jimmy,” he moans. “Please fuck me.”

“What about me, little prince?” Castiel growls in Dean’s ear, and Dean quickly puts his hands on as much of Castiel as he can.

“I want you to fuck me, too, but Jimmy’s already working on it, I guess.”

At that, one of Castiel’s tentacles joins Jimmy’s and Dean has a hard time keeping the triumphant smile from his face. Of course it was his goal to have Cas in him, too, and the twins are always ready to give him what he wants, but sometimes Dean just doesn’t know how to ask for things. As the twins move in tandem, opening Dean up further to take both of their dicks, Dean occupies himself by kissing Cas and then Jimmy. He’s had both dicks in him before, and he knows that he needs to distract himself for a little bit, but it doesn’t take long before the twins’ large erections are inside him. They never last long if they are both inside of him, and that simply tells Dean that they love both him and each other.

When they are getting close, they wrap tentacles around Dean’s dick, too, and jerk him off in the same fast pace that they’ve set for their thrusts, and Dean comes seconds before Cas and Jimmy. His come floats into the ocean, while the twins fill him with warm semen – a lot of it, since apparently they produce more than the average human. Dean doesn’t mind. He loves the feeling of being full of the twins’ seed for longer, and he hates having to get out of the water, to go to sleep in his own bed and be alone for the entire night.

He still has to say goodbye to the twins, though, and when his muscles are getting tired, the twins help him back onto the pier and watch him until they are sure he’s safely in bed. Dean loves them, and he knows they love him, too. Them living together might not be perfect, but it’s good enough for now, and there’ll be improvements as they go along.

****

The abduction of Dean Winchester, crown prince to the kingdom, is the biggest news for a year. After that, people remember, of course, but stop meting it out so big in the news. His brother, Sam, is trained to take over at that point, and he’ll manage just fine, especially with his fiancée Jess. They’re a great couple, and it might actually be a good thing that Dean disappeared. He wasn’t fit to rule the human world anyway.


	4. Day 4: Books/Daddy+Gags [bonus prompt: mantis]

**Summary for the Chapter:**

> Welp, a Dean/Cas/Benny day!
> 
> Suptober: Books  
Kinktober: Daddy + Gags  
Mantistober: Mantis

**Notes for the Chapter:**

> Rating: Explicit  
Ship: Dean/Cas/Benny  
Tags: daddy!kink, sub!dean, sub!cas, dom!benny

Castiel’s library has been a mess since they moved. Castiel hasn’t had time to actually get around to sorting the books, and Benny has been implying that it needs to get done ever since he tripped over a random book on the mantis, of all things, and almost broke his elbow on the windowsill in his fall. They simply haven’t gotten around to it. Plus, Castiel had a very particular system in setting up his books, and even if Dean and Benny had attempted at some point to put books in the cases and on the shelves, they would have been removed the day after because they weren’t in the right position.

Benny has come up with a great idea, though – they set up a weekend where they wouldn’t be bothered, and he’d simply Dom them into finally getting the books set up correctly. During scenes, Dean craved order and simplicity, and Castiel was the brat of the two. However, organising his own library would keep him calm – or at least, Benny hoped that was how it was going to work out. After some talking, they decided that they’d do this naked, because Benny complained that the scene wouldn’t really do a lot for him. He liked to at least be able to look at his two beautiful subs while they were cleaning up a space that definitely needed that kind of attention.

When weekend finally arrives, the three are ready. They’ve had challenging weeks and are looking forward to relaxing in their own way. Benny has dragged an arm chair into the library for him to sit in during the scene and observe his subs while they work. He doesn’t think he’ll need to do an awful lot, but who knows at this point. They can act out, and will amplify each other if they do. So Benny _does _need to keep an eye on them. He leads his boys into the library once they’re undressed – and Benny pretends that he hasn’t seen Dean slip a plug into his ass – and sits them down on the floor.

“Are you ready to get your work done today?” Benny asks. Both Dean and Cas nod, of course. “Good boys… So I want Castiel to explain his shelving system, and Dean, you can sort the books alphabetically so that it’s easier for Cas to find the book he wants. Is that okay?”

“Yes, daddy,” both Dean and Castiel mumble.

“Thank you,” Benny says. “I have one more addition: Dean, I saw you putting in the plug.” Dean flushes, but he doesn’t apologise for not following Benny’s instructions to the letter. “You will be gagged as a punishment. I don’t want to hear you complain about how long you’re going to have to keep it in because you didn’t think this through. Is that understood, boy?”

Dean nods, his entire face red, but Benny knows that it’s probably flushed in excitement rather than embarrassment.

“You know I want verbal acknowledgement, Dean.”

“Yes, daddy,” Dean whispers. “I will wear the gag.”

“Thank you. Good boy.” Benny pulls the panties Cas wore that night from the pocket in his sweat pants and shoves them into Dean’s mouth. “I hope you enjoy Castiel’s flavour.” Benny licks his lips and claps his hands together. “Well, let’s get started! We don’t want to be in this room for the entire weekend, now do we? Let’s get this room sorted out!”


	5. Day 5:  Water/Frotting

**Summary for the Chapter:**

> Day 5  
Suptober: Water  
Kinktober: Frotting

**Notes for the Chapter:**

> Here we go again! I should probably mention that these are unbeta'd and usually written in the span of an hour, soooo....
> 
> Ship: DeanCasJimmy  
Rating: explicit  
Tags: frotting, Jimmy and Dean are dating, Jimmy and Cas are dating, Cas and Jimmy are twins, technically some adultery but it's okay because it's all leading up to dcj

Dean and Jimmy have been dating for the longest time, and Dean knows that he should have simply told Jimmy that he might be interested in his brother too, but he didn’t. Not until it actually mattered, of course.

One night, there is a party, as is often the case, but this one is attended by… many people. Dean doesn’t even discuss going with Jimmy, knowing that Jimmy will probably have started advertising the party himself at this point. Dean knows, too, that Castiel won’t be there. Castiel is the more bookish of the twins, often spending his evenings catching up on some reading that he couldn’t do during the weekdays. Dean loves the fact that Castiel is such a homebody and that he’s able to tell people (especially Jimmy) no when they ask him to come out and party with them.

So no, Dean is not expecting Cas to be there. Dean has been lounging near the pool, which he discovered after a few bottles of beer, and he’s enjoying the water, talking to a few of his friends. When he spots Jimmy, though, he gets up. His friends look at him, wiggling their eyebrows at him with this uncanny unity, and shoo him away. They definitely know not to expect him back before he’s greeted his boyfriend.

Dean might be slightly… tipsy, to say the least, but that doesn’t mean he can’t spot the difference between Cas and Jimmy. He’s always been good at telling the difference between the twins – uncannily so, according to his friends – and he knows, seconds after putting his hand on the twin’s shoulder, that this is Castiel, rather than Jimmy.

“Hey Cas,” Dean says.

Castiel smiles up at him. “Hello Dean.”

Dean unconsciously licks his lips and then bites his lower lip. “I didn’t think you’d be here. Where’s Jimmy?”  
“Jimmy couldn’t make it today,” Cas says. “I’m here as a stand in.”

“People will know that it’s not Jimmy, though.” Although Dean knows a quick solution to make them all think that it is, in fact, Jimmy who is with him. _He shouldn’t, though_. Definitely not. Bad idea if he ever had one.

Castiel shrugs. “I don’t care. Jimmy shouldn’t have asked me to step in, then.”

“How did he get you to join?”

“He’ll buy me five books.” Castiel shrugs again. “He thinks it’s not a big deal, but I’ve had my eye on a few rare books. It’s going to cost him more than he thinks.”

Dean laughs at that. He should have known that it was going to cost Jimmy more than Jimmy himself thought it would cost. Silence falls between the two, and Dean is suddenly aware of the fact that they are still standing near the pool. Rather awkwardly, even. Dean grabs Castiel’s upper arm and leads him into the house.

“If you’re posing as Jimmy, you should at least hold a beer.” Dean doesn’t say that his fingers are tingling from contact with Cas, he doesn’t say that everyone has probably already figured out that this definitely isn’t Jimmy. Because Jimmy would have kissed Dean with enthusiasm, and Cas hasn’t made a move. Dean cannot, he _cannot_, be sad about the fact that Cas doesn’t want to kiss him.

Cas grabs a bottle of vodka and takes over leading duty from Dean, leading them to a much quieter spot somewhere in the garden. They sit and drink and talk, and Dean is drunk by the time the bottle is empty, and even though Cas drank the majority of the vodka, he doesn’t appear to be affected at all.

Dean is slurring, he doesn’t even know what he’s saying anymore. He has a vague sense that he’s talking about something that he maybe shouldn’t say to Cas but Cas is his best friend, like Jimmy is, and he doesn’t want there to be any secrets between them. He just knows that they’ve shifted closer and that he likes it, and that he’s flushed – whether from alcohol or something else, he doesn’t know. Castiel’s face is much closer now, and Dean simply wants to press a kiss to his lips _so bad_.

So he does.

At first, Castiel doesn’t react whatsoever, and Dean is getting himself ready to apologise and move on, but then Castiel’s lips start moving and it is _glorious_.

“Fucking finally,” Castiel sighs between kisses, and although Dean wants to know more about that, he doesn’t ask. Doesn’t get the chance to ask, because Cas is claiming his lips again, running his fingers over Dean’s body and moving slowly towards the growing bulge, still hidden by Dean’s jeans. Dean pushes his hips into Castiel’s hand, and Cas knows what he wants, but apparently elects to ignore it.

Both of Castiel’s hands are busy exploring Dean’s shoulders, now, and Dean is very much confused when two hands join and shove Dean’s jeans down his ass.

“Wha--”

“Hello Dean,” a voice rumbles near his ear. A voice he damn well recognises.

“Jimmy,” Dean exhales. He doesn’t dare turn around, afraid to face his boyfriend now that he’s actively fondling said boyfriend’s identical twin brother.

“I see you’ve finally acted on this hidden desire of yours,” Jimmy says. Dean was already flushed, but he’s sure the embarrassment is causing his flush to deepen and spread even further. He didn’t want the twins to know that he liked _both _of them, because that’s simply weird, right? But Jimmy just continued working Dean’s pants off without waiting for Dean’s reply, and he’s clearly interested, judging by the erection that is poking Dean’s backside.

“Hello brother,” Castiel rasps when they finally break their kiss long enough to actually speak. “Nice of you to join us.”

“Nice of you to invite me, Cas,” Jimmy says, a smile clear in his voice. “I wish Dean had just told me, but this is a good way to introduce him to our relationship too, right?”

Cas leans over to kiss Jimmy, humming in agreement. “Dean, Jimmy and I have been together since we were fourteen. I’m sorry we hid this from you, but well… up until this point, we weren’t quite sure if you were even open to sharing Jimmy, so we simply didn’t tell you.”  
“You fuck?” Dean asks, breathless, as he watches Cas undo his own pants and shove them down to sit around his ankles. He’s being sandwiched by the twins and is hoping with all he has that this is not some kind of weird dream.

“We do,” Jimmy says. “And we want to include you in that. We should talk about this when we’re all sober, and then we can discuss your reactions.”

Dean simply nods and moans as Castiel’s cock rubs against his own and Jimmy’s against his ass. It’s dry and not the best ever, but it gets the job done. All three come in quick succession, and sigh when they come down from their highs. They quickly clean themselves off and then drag themselves home. The discussion can wait, but they do want to spend the night together, at least.


End file.
